Pyrazolopyrimidine nucleosides. 12. Synthesis and biological activity of certain pyrazolo [3, 4-d] pyrimidine nucleosides related to adenosine

…, RP Panzica, LL Wotring, LB Townsend

Index: Bhat; Montero; Panzica; Wotring; Townsend Journal of Medicinal Chemistry, 1981 , vol. 24, # 10 p. 1165 - 1172

Full Text: HTML

Citation Number: 47

Abstract

The chemical synthesis of certain 4-substituted pyrazolo [3, 4-d] pyrimidine nucleosides is described. Using 1-(2, 3,~ tri-O-acetyl-~ Dribofuranosyl) pyraZ(1) as the starting material, the reactive intermediate 4-chloro-l-(2, 3, 5-tri-O-acetyl-&D-ribofuran(2) was prepared in excellent yield. Compound 2 served as a versatile precursor for the synthesis of a number of 4-substituted pyrazolo [3, 4-d] pyrimidine nucleosides. In antitumor studies of these ...

 Related Synthetic Route
N,N-Dimethylformamide dimethyl acetal Structure

4637-24-5

N,N-Dimethylfor...

1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 1-.beta.-D-ribofuranosyl- Structure

3258-05-7

1H-Pyrazolo[3,4...

~81%

Methanimidamide,N,N-dimethyl-N'-(1-b-D-ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)- Structure

78586-44-4

Methanimidamide...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

Methanimidamide,N,N-dimethyl-N'-(1-b-D-ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)- Structure

78586-44-4

Methanimidamide...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~%

Methanimidamide,N,N-dimethyl-N'-(1-b-D-ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)- Structure

78586-44-4

Methanimidamide...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~87%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 1-.beta.-D-ribofuranosyl- Structure

3258-05-7

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 1-.beta.-D-ribofuranosyl- Structure

3258-05-7

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,1-(5-O-acetyl-b-D-ribofuranosyl)-N-(phenylmethyl)- Structure

78586-37-5

1H-Pyrazolo[3,4...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

Benzylamine Structure

100-46-9

Benzylamine

~38%

2-[5-(benzylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-36-4

2-[5-(benzylami...

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,1-(5-O-acetyl-b-D-ribofuranosyl)-N-(phenylmethyl)- Structure

78586-37-5

1H-Pyrazolo[3,4...

Methyl mercaptan Structure

74-93-1

Methyl mercaptan

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~72%

1H-Pyrazolo[3,4-d]pyrimidine,4-(methylthio)-1-b-D-ribofuranosyl- Structure

60355-67-1

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidine,4-(methylthio)-1-b-D-ribofuranosyl- Structure

60355-67-1

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

[5-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-3,4-dihydroxy-oxolan-2-yl]methyl acetate Structure

78586-39-7

[5-[5-(2-furylm...

Furfurylamine Structure

617-89-0

Furfurylamine

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~35%

2-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-38-6

2-[5-(2-furylme...

[5-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-3,4-dihydroxy-oxolan-2-yl]methyl acetate Structure

78586-39-7

[5-[5-(2-furylm...

1H-Pyrazolo[3,4-d]pyrimidine,4-(methylthio)-1-b-D-ribofuranosyl- Structure

60355-67-1

1H-Pyrazolo[3,4...

~%

2-(hydroxymethyl)-5-(2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)oxolane-3,4-diol Structure

78586-40-0

2-(hydroxymethy...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

2-(hydroxymethyl)-5-(2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)oxolane-3,4-diol Structure

78586-40-0

2-(hydroxymethy...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~%

2-(hydroxymethyl)-5-(2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)oxolane-3,4-diol Structure

78586-40-0

2-(hydroxymethy...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

Dimethylamine Structure

124-40-3

Dimethylamine

~90%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,N,N-dimethyl-1-b-D-ribofuranosyl- Structure

64372-75-4

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,N,N-dimethyl-1-b-D-ribofuranosyl- Structure

64372-75-4

1H-Pyrazolo[3,4...

[3,4-diacetyloxy-5-(5-anilino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-34-2

[3,4-diacetylox...

~90%

2-(5-anilino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-35-3

2-(5-anilino-2,...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

2-(5-anilino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-35-3

2-(5-anilino-2,...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

1-methyl-4-nitro-5-mercaptoimidazole ammonium salt Structure

13750-88-4

1-methyl-4-nitr...

~95%

1H-Pyrazolo[3,4-d]pyrimidine,4-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

78586-42-2

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidine,4-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

78586-42-2

1H-Pyrazolo[3,4...

Sodium Methylate Structure

124-41-4

Sodium Methylate

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~97%

1-.beta.-D-ribofuranosyl-4-methoxypyrazolo[3,4-d] pyrimidine Structure

70421-26-0

1-.beta.-D-ribo...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1-.beta.-D-ribofuranosyl-4-methoxypyrazolo[3,4-d] pyrimidine Structure

70421-26-0

1-.beta.-D-ribo...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~%

2-(5-anilino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-35-3

2-(5-anilino-2,...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1-b-D-ribofuranosyl-, hydrazone(9CI) Structure

64372-76-5

4H-Pyrazolo[3,4...

Benzaldehyde,4-[bis(2-chloroethyl)amino]- Structure

1208-03-3

Benzaldehyde,4-...

~81%

2-[5-[2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-43-3

2-[5-[2-[[4-[bi...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

2-[5-[2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-43-3

2-[5-[2-[[4-[bi...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~%

2-[5-[2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-43-3

2-[5-[2-[[4-[bi...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

methylamine Structure

74-89-5

methylamine

~92%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,N-methyl-1-b-D-ribofuranosyl- Structure

64372-74-3

1H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,N-methyl-1-b-D-ribofuranosyl- Structure

64372-74-3

1H-Pyrazolo[3,4...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~71%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1-b-D-ribofuranosyl-, hydrazone(9CI) Structure

64372-76-5

4H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1-b-D-ribofuranosyl-, hydrazone(9CI) Structure

64372-76-5

4H-Pyrazolo[3,4...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

2-[5-(benzylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-36-4

2-[5-(benzylami...

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,1-(5-O-acetyl-b-D-ribofuranosyl)-N-(phenylmethyl)- Structure

78586-37-5

1H-Pyrazolo[3,4...

~%

2-[5-(benzylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-36-4

2-[5-(benzylami...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~%

2-[5-(benzylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-36-4

2-[5-(benzylami...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

Benzylamine Structure

100-46-9

Benzylamine

~41%

2-[5-(benzylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-36-4

2-[5-(benzylami...

1H-Pyrazolo[3,4-d]pyrimidin-4-amine,1-(5-O-acetyl-b-D-ribofuranosyl)-N-(phenylmethyl)- Structure

78586-37-5

1H-Pyrazolo[3,4...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

Structure

74497-02-2

~68%

[3,4-diacetyloxy-5-(5-anilino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-34-2

[3,4-diacetylox...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

[3,4-diacetyloxy-5-(5-anilino-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-34-2

[3,4-diacetylox...

4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5-dihydro-1-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)- Structure

64372-69-6

4H-Pyrazolo[3,4...

~%

2-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-38-6

2-[5-(2-furylme...

[5-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-3,4-dihydroxy-oxolan-2-yl]methyl acetate Structure

78586-39-7

[5-[5-(2-furylm...

~%

2-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-38-6

2-[5-(2-furylme...

Furfurylamine Structure

617-89-0

Furfurylamine

~%

2-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-38-6

2-[5-(2-furylme...

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~%

2-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-38-6

2-[5-(2-furylme...

Furfurylamine Structure

617-89-0

Furfurylamine

[3,4-diacetyloxy-5-(5-chloro-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,7,10-tetraen-9-yl)oxolan-2-yl]methyl acetate Structure

78586-33-1

[3,4-diacetylox...

~41%

2-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Structure

78586-38-6

2-[5-(2-furylme...

[5-[5-(2-furylmethylamino)-2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,5,7-tetraen-9-yl]-3,4-dihydroxy-oxolan-2-yl]methyl acetate Structure

78586-39-7

[5-[5-(2-furylm...


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